Hydrazine → (2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazide

(4S)-3-{(2S)-2-[(S)-[3,5-Bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enoyl}-4-phenyl-1,3-oxazolidin-2-one (20 g, 42.5 mmol) and hydrazine (2.71 g, 85 mmol) in THF (100 mL) was stirred at room temperature for 1 hour. The reaction was diluted with ethyl acetate:hexanes (2:1, 200 mL) and was partitioned with water (100 mL). The organic was washed with brine (100 mL) and was dried over sodium sulfate, filtered, and concentrated. The crude product was triturated with IPA (30 mL) to remove the chiral auxiliary. The filtrate was concentrated to yield (2S)-2-[(S)-[3,5-bis(trifluoromethyl)phenyl](hydroxy)methyl]but-3-enehydrazide (14.5 g, 42.4 mmol), which was used without further purification. 1H NMR (500 MHz, CDCl3) δ7.81 (s, 3H), 7.83 (s, 1H), 7.0 (br s, 1H), 5.9 (m, 1H), 5.42 (d, J=3.3 Hz, 1H), 5.29 (d, J=10.3 Hz, 1H), 5.03 (d, J=17.1 Hz, 1H), 3.1 (dd, J=9.4, 3.5 Hz, 1H).

1. customwas partitioned with water (100 mL)
2. washThe organic was washed with brine (100 mL)
3. dry with materialwas dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was triturated with IPA (30 mL)
7. customto remove the chiral auxiliary
8. concentrationThe filtrate was concentrated

ORD record

ord-4219424d90d0400194b0fc7d65e01753

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346825B2